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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32O5
Molecular Weight 352.4651
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of 8-ISOPROSTAGLANDIN E2

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=XEYBRNLFEZDVAW-CLQOMRTCSA-N
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,19+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15650411 | https://www.ncbi.nlm.nih.gov/pubmed/26209241 | https://www.ncbi.nlm.nih.gov/pubmed/9717718 |

8-Iso-prostaglandin E2 (8-iso-PGE2) is one of the several isoprostanes produced from arachidonic acid during lipid peroxidation. Isoprostanes are a group of stable prostaglandin-like compounds produced by free radical-catalyzed, non-enzymatic peroxidation of arachidonic acid, which are used as markers of oxidative stress in several human diseases, including diabetes. In addition, 8-iso-prostaglandin E2 is biologically active compound involved in contraction of vascular smooth muscle and activation of platelets. 8-iso-PGE2 has been demonstrated to be the most potent vasoconstrictor isoprostane on the human umbilical artery and vein, activating the TPα isoform, which is present in the human umbilical vein and platelets. 8-iso-prostaglandin E2 stimulates human umbilical vein endothelial cells to specifically bind monocytes and this effect is mediated by cyclic AMP/protein kinase A- and p38 MAP kinase-dependent pathways and is independent of the classical inflammatory NFkappaB pathway.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Isoprostanes as physiological mediators of transition to newborn life: novel mechanisms regulating patency of the term and preterm ductus arteriosus.
2012 Aug
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Human umbilical cords were collected from healthy and normotensive women after full-term vaginal or caesarean deliveries. Cumulative concentration-response curves to 8-iso-PGE2 were obtained by addition to the organ bath in 0.25 log10 increments (1, 1.7, 3, 5.5, and 10 nmol/l etc. to 30 μmol/l). Concentrationresponse curves to 8-iso-PGE2 were obtained alone and in the presence of EV-077 (1, 3, 10 and 30 nmol/l) added to the solution 30 min before the agonist. At the end of each concentration-response curve, serotonin (5-HT, 10 μmol/l) was applied to determine the tissue maximal contractile response. The isoprostane 8-iso-PGE2 evoked concentration-dependent contraction of the human umbilical artery, yielding a pEC50 value of 7.33±0.05
Name Type Language
8-ISOPROSTAGLANDIN E2
Common Name English
PROSTA-5,13-DIEN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (5Z,8.BETA.,11.ALPHA.,13E,15S)-
Systematic Name English
DINOPROSTONE IMPURITY, 8-ISODINOPROSTONE- [USP IMPURITY]
Common Name English
(Z)-7-((1S,2R,3R)-3-HYDROXY-2-((E)-(3S)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENTYL)HEPT-5-ENOIC ACID
Systematic Name English
DINOPROSTONE IMPURITY B [EP IMPURITY]
Common Name English
8-ISO-PGE2
Common Name English
15-E2T-ISOPROSTANE
Common Name English
8-ISODINOPROSTONE
Common Name English
Code System Code Type Description
FDA UNII
W1ANC8Q5NW
Created by admin on Sat Dec 16 09:30:54 GMT 2023 , Edited by admin on Sat Dec 16 09:30:54 GMT 2023
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CHEBI
131888
Created by admin on Sat Dec 16 09:30:54 GMT 2023 , Edited by admin on Sat Dec 16 09:30:54 GMT 2023
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CAS
27415-25-4
Created by admin on Sat Dec 16 09:30:54 GMT 2023 , Edited by admin on Sat Dec 16 09:30:54 GMT 2023
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EPA CompTox
DTXSID701024826
Created by admin on Sat Dec 16 09:30:54 GMT 2023 , Edited by admin on Sat Dec 16 09:30:54 GMT 2023
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PUBCHEM
5283213
Created by admin on Sat Dec 16 09:30:54 GMT 2023 , Edited by admin on Sat Dec 16 09:30:54 GMT 2023
PRIMARY